CA1138864A - 4-phenyl-4,5,6,7-tetrahydro-pyrrolo[2,3-c] pyridines, process for the production thereof and pharmaceutical compositions - Google Patents
4-phenyl-4,5,6,7-tetrahydro-pyrrolo[2,3-c] pyridines, process for the production thereof and pharmaceutical compositionsInfo
- Publication number
- CA1138864A CA1138864A CA000355540A CA355540A CA1138864A CA 1138864 A CA1138864 A CA 1138864A CA 000355540 A CA000355540 A CA 000355540A CA 355540 A CA355540 A CA 355540A CA 1138864 A CA1138864 A CA 1138864A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- bromophenyl
- pyrrolo
- tetrahydro
- pyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims 10
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 4
- YYLVBYQDRJYOTK-UHFFFAOYSA-N 4-phenyl-4,5,6,7-tetrahydro-1h-pyrrolo[2,3-c]pyridine Chemical class C1NCC=2NC=CC=2C1C1=CC=CC=C1 YYLVBYQDRJYOTK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 239000000460 chlorine Chemical group 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 239000011737 fluorine Chemical group 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- -1 alkyl radical Chemical class 0.000 claims description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 11
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 10
- 229960000583 acetic acid Drugs 0.000 claims description 7
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- NNINSLOEPXEZOZ-UHFFFAOYSA-N 2-(4-bromophenyl)oxirane Chemical compound C1=CC(Br)=CC=C1C1OC1 NNINSLOEPXEZOZ-UHFFFAOYSA-N 0.000 claims description 4
- GYNPKCPHHBWISN-UHFFFAOYSA-N 4-(4-bromophenyl)-1,3,6-trimethyl-2-piperidin-1-yl-5,7-dihydro-4H-pyrrolo[2,3-c]pyridine Chemical compound CN1C(=C(C2=C1CN(CC2C2=CC=C(C=C2)Br)C)C)N2CCCCC2 GYNPKCPHHBWISN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 claims 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 125000001246 bromo group Chemical group Br* 0.000 claims 8
- LNVJOEISRQDAHH-UHFFFAOYSA-N 4-(4-bromophenyl)-1,3,6-trimethyl-2-pyrrolidin-1-yl-5,7-dihydro-4H-pyrrolo[2,3-c]pyridine Chemical compound CN1C(=C(C2=C1CN(CC2C2=CC=C(C=C2)Br)C)C)N2CCCC2 LNVJOEISRQDAHH-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- CWLOFLFPSNCBFN-UHFFFAOYSA-N 2-bromo-4-(4-bromophenyl)-1,6-dimethyl-5,7-dihydro-4h-pyrrolo[2,3-c]pyridine Chemical compound C1=2C=C(Br)N(C)C=2CN(C)CC1C1=CC=C(Br)C=C1 CWLOFLFPSNCBFN-UHFFFAOYSA-N 0.000 claims 2
- WIBUSVGJVAYNBU-UHFFFAOYSA-N 4-(4-bromophenyl)-1,6-dimethyl-5,7-dihydro-4h-pyrrolo[2,3-c]pyridine Chemical compound C1=2C=CN(C)C=2CN(C)CC1C1=CC=C(Br)C=C1 WIBUSVGJVAYNBU-UHFFFAOYSA-N 0.000 claims 2
- HQVOLDSMHIXLGI-UHFFFAOYSA-N 4-(4-bromophenyl)-1-methyl-4,5,6,7-tetrahydropyrrolo[2,3-c]pyridine Chemical compound C1NCC=2N(C)C=CC=2C1C1=CC=C(Br)C=C1 HQVOLDSMHIXLGI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 abstract description 6
- 230000001430 anti-depressive effect Effects 0.000 abstract description 5
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- 239000004480 active ingredient Substances 0.000 description 9
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- 238000005893 bromination reaction Methods 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 210000004720 cerebrum Anatomy 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229950006768 phenylethanolamine Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2927294.4 | 1979-07-06 | ||
| DE19792927294 DE2927294A1 (de) | 1979-07-06 | 1979-07-06 | Neue 4-phenyl-4,5,6,7-tetrahydropyrrolo eckige klammer auf 2,3-c eckige klammer zu pyridine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1138864A true CA1138864A (en) | 1983-01-04 |
Family
ID=6075042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000355540A Expired CA1138864A (en) | 1979-07-06 | 1980-07-04 | 4-phenyl-4,5,6,7-tetrahydro-pyrrolo[2,3-c] pyridines, process for the production thereof and pharmaceutical compositions |
Country Status (26)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5890951A (ja) * | 1981-11-26 | 1983-05-30 | 住友金属工業株式会社 | 耐食性にすぐれた積層板 |
| JPS59193175A (ja) * | 1983-04-19 | 1984-11-01 | Toa Nenryo Kogyo Kk | 積層物 |
| US4572911A (en) * | 1984-08-02 | 1986-02-25 | Mcneilab, Inc. | Hexahydroindolinzine compounds, pharmaceutical compositions and methods and intermediates |
| EP4003339A4 (en) * | 2019-07-30 | 2023-02-22 | Sanford Burnham Prebys Medical Discovery Institute | DOPAMINE RECEPTOR D1 AGONISTS AND METHODS OF USE |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1484140A (en) * | 1974-04-24 | 1977-08-24 | Wyeth John & Brother Ltd | Pyrrolopyridine derivatives |
| AT368504B (de) * | 1977-10-15 | 1982-10-25 | Boehringer Sohn Ingelheim | Verfahren zur herstellung neuer 4-phenyl-thieno- (2,3-c)-piperidine |
-
1979
- 1979-07-06 DE DE19792927294 patent/DE2927294A1/de not_active Withdrawn
-
1980
- 1980-06-30 IT IT23120/80A patent/IT1150024B/it active
- 1980-06-30 US US06/163,969 patent/US4315938A/en not_active Expired - Lifetime
- 1980-07-02 AT AT0344680A patent/AT375077B/de not_active IP Right Cessation
- 1980-07-03 CH CH5125/80A patent/CH649548A5/de not_active IP Right Cessation
- 1980-07-03 YU YU01747/80A patent/YU174780A/xx unknown
- 1980-07-03 GR GR62353A patent/GR69327B/el unknown
- 1980-07-04 ZA ZA00804031A patent/ZA804031B/xx unknown
- 1980-07-04 SE SE8004976A patent/SE436747B/sv unknown
- 1980-07-04 HU HU801678A patent/HU182152B/hu unknown
- 1980-07-04 NO NO802014A patent/NO802014L/no unknown
- 1980-07-04 ES ES493104A patent/ES493104A0/es active Granted
- 1980-07-04 FR FR8015010A patent/FR2460950A1/fr active Granted
- 1980-07-04 NL NL8003879A patent/NL8003879A/nl not_active Application Discontinuation
- 1980-07-04 LU LU82582A patent/LU82582A1/de unknown
- 1980-07-04 BE BE0/201313A patent/BE884193A/fr not_active IP Right Cessation
- 1980-07-04 IL IL60499A patent/IL60499A/xx unknown
- 1980-07-04 CA CA000355540A patent/CA1138864A/en not_active Expired
- 1980-07-04 AU AU60138/80A patent/AU536336B2/en not_active Ceased
- 1980-07-04 PT PT71500A patent/PT71500B/pt unknown
- 1980-07-04 DK DK290380A patent/DK290380A/da not_active Application Discontinuation
- 1980-07-04 GB GB8022046A patent/GB2054580B/en not_active Expired
- 1980-07-04 NZ NZ194245A patent/NZ194245A/en unknown
- 1980-07-04 JP JP9161580A patent/JPS5610184A/ja active Pending
- 1980-07-04 FI FI802148A patent/FI802148A7/fi not_active Application Discontinuation
- 1980-07-07 PH PH24246A patent/PH15756A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT375077B (de) | 1984-06-25 |
| AU536336B2 (en) | 1984-05-03 |
| CH649548A5 (de) | 1985-05-31 |
| JPS5610184A (en) | 1981-02-02 |
| SE8004976L (sv) | 1981-01-07 |
| IT8023120A0 (it) | 1980-06-30 |
| IL60499A (en) | 1984-02-29 |
| LU82582A1 (de) | 1981-09-10 |
| HU182152B (en) | 1983-12-28 |
| IL60499A0 (en) | 1980-09-16 |
| NL8003879A (nl) | 1981-01-08 |
| NZ194245A (en) | 1984-07-06 |
| PT71500B (de) | 1981-12-11 |
| FR2460950A1 (fr) | 1981-01-30 |
| FI802148A7 (fi) | 1981-01-01 |
| DE2927294A1 (de) | 1981-01-08 |
| NO802014L (no) | 1981-01-07 |
| FR2460950B1 (cg-RX-API-DMAC10.html) | 1983-06-24 |
| GB2054580A (en) | 1981-02-18 |
| BE884193A (fr) | 1981-01-05 |
| DK290380A (da) | 1981-01-07 |
| ATA344680A (de) | 1983-11-15 |
| GB2054580B (en) | 1983-04-07 |
| GR69327B (cg-RX-API-DMAC10.html) | 1982-05-17 |
| US4315938A (en) | 1982-02-16 |
| ES8201019A1 (es) | 1981-11-01 |
| AU6013880A (en) | 1981-01-15 |
| IT1150024B (it) | 1986-12-10 |
| ZA804031B (en) | 1982-03-31 |
| SE436747B (sv) | 1985-01-21 |
| YU174780A (en) | 1983-02-28 |
| PT71500A (de) | 1980-08-01 |
| PH15756A (en) | 1983-03-18 |
| ES493104A0 (es) | 1981-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |